Home / Journeys / The Grand American Drive, Route 66 Edition

14 nights · Chicago, United States → Santa Monica, United States · Car

The Grand American Drive, Route 66 Edition

Drive the whole of Route 66 in its centenary year and arrive in Las Vegas for Grand Prix weekend.

From£6,181pp

Duration14 days

StyleGuided

Best suited toDrivers who want the road to be the holiday

Find out more

An independent Stradora pick. Details from the operator's published information, last checked 28 Oct 2026. Stradora DiscoveryChosen independently by our editors because we think it's worth the drive. We're not partnered with this operator: dates, prices and booking are handled by them, and we last checked their published details on 28 Oct 2026.

Booked with the operator?

Tell us your trip details and we'll put together a complimentary Stradora Expedition Pack for the journey.

Claim your pack

14 nights through United States

Fourteen nights from Chicago to Santa Monica, escorted self-drive, more than four thousand kilometres of Route 66 over eleven driving days.

The whole road, end to end, in its centenary period: Route 66 was commissioned in 1926 and the November departure is timed to arrive in Las Vegas for the Grand Prix weekend, which gives the trip two endings rather than one.

Chicago opens it, with a day in the city and the start of the road. St Louis follows, then Springfield by way of the Ozarks, Oklahoma City, and Amarillo with the Cadillac Ranch, where ten cars stand nose-down in a field. Albuquerque comes next with a round trip to Santa Fe, then Holbrook across the Painted Desert, Page, and Williams by way of the Grand Canyon. Las Vegas follows past the Hoover Dam, with the Grand Prix weekend and F1 tickets available separately, and the final day crosses the Mojave to Santa Monica and the end of the road at the pier.

The cars are provided, shared between two guests, from a BMW X3 or Mercedes C-Class to a Jeep Wrangler; the full inclusions were not itemised on the operator’s page and are worth confirming at booking, and the Grand Prix tickets and hospitality are an optional extra. The price shown is per person sharing. The November dates are set by the race, which is also the best time of year to be crossing Arizona and the Mojave. Fifteen days for the full length of the road is the right allocation.

Style

Guided, Luxury

Duration

A fortnight (11-15 nights)

Region

North America

Vehicle provision

Vehicle provided

Group size

Departures

November

Starts/ends

Chicago, United States → Santa Monica, United States

Support

Guide

Suitable cars

Drivers who want the road to be the holiday

Vehicle

Car

Price basis

Per person (sharing)

Run by

Independent specialist operator

The Grand American Drive, Route 66 Edition (1 of 8)

Route 66 shield painted on the road at sunrise in the Mojave Desert

The Grand American Drive, Route 66 Edition (2 of 8)

Roy's Motel and Cafe neon sign on Route 66 in Amboy, California

The Grand American Drive, Route 66 Edition (3 of 8)

Vintage gas station with blue pumps in the Arizona desert

Images selected by Stradora to represent the journey.

Day by Day